Dimethyl Sulfide → (2-Ethoxy-2-oxoethyl)dimethylsulphonium bromide

A stirred solution of ethyl bromoacetate (98%, 287 g, 1.68 mol) and methyl sulfide (99%, 156 mL, 1.25 eq.) in acetone (500 mL) was kept at 15° C. A white precipitate started to appear immediately and became thicker upon stirring. After stirring for 18 h at 22° C., the solid was filtered, washed with acetone (3×100 mL), and dried under vacuum to afford 1 (477 g, 83.4%) as white crystals. 1H NMR (250 MHz, CDCl3) δ 5.20 (s, 2H); 4.29 (q, J=7.2, 2H); 3.46 (s, 6H); 1.32 (t, J=7.2, 3H). 13C NMR (62.5 MHz, CDCl3) δ 164.36; 63.38; 44.38; 25.22; 13.92.

1. customwas kept at 15° C
2. stirringAfter stirring for 18 h at 22° C.
3. filtrationthe solid was filtered
4. washwashed with acetone (3×100 mL)
5. customdried under vacuum

ORD record

ord-09a9dbf030b6474c95c16db7d2a41a03

Source dataset

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07453011B2